S$179 Cheap Flights from Toronto to Chicago

View S$179 flight on Fri, 24 Oct, 2025Opens in a new window

Popular airlines from Toronto Pearson Intl. Airport (YYZ) to Chicago Midway Airport (MDW)

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Cheap Flights from Toronto to Chicago (YYZ-MDW)

Prices were available within the past 7 days and start at S$179 for one-way flights and S$297 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 6 Aug - Wed, 13 Aug
YYZ
Toronto
MDW
Chicago
S$297 Return, found 3 days ago
S$297
Return
found 3 days ago
Select Delta flight, departing Wed, 6 Aug from Toronto to Chicago, returning Wed, 13 Aug, priced at S$297 found 3 days ago
Delta
Wed, 6 Aug - Wed, 13 Aug
YYZ
Toronto
MDW
Chicago
S$417 Return, found 3 days ago
S$417
Return
found 3 days ago
Select Delta flight, departing Wed, 6 Aug from Toronto to Chicago, returning Wed, 13 Aug, priced at S$417 found 3 days ago
Delta
Wed, 6 Aug - Wed, 13 Aug
YYZ
Toronto
MDW
Chicago
S$454 Return, found 3 days ago
S$454
Return
found 3 days ago
Select Delta flight, departing Wed, 6 Aug from Toronto to Chicago, returning Wed, 13 Aug, priced at S$454 found 3 days ago
Delta
Wed, 6 Aug - Wed, 13 Aug
YYZ
Toronto
MDW
Chicago
S$468 Return, found 3 days ago
S$468
Return
found 3 days ago
Select Delta flight, departing Wed, 6 Aug from Toronto to Chicago, returning Wed, 13 Aug, priced at S$468 found 3 days ago
Delta
Wed, 6 Aug - Wed, 13 Aug
YYZ
Toronto
MDW
Chicago
S$506 Return, found 3 days ago
S$506
Return
found 3 days ago
Select Delta flight, departing Wed, 6 Aug from Toronto to Chicago, returning Wed, 13 Aug, priced at S$506 found 3 days ago
Delta
Wed, 6 Aug - Wed, 13 Aug
YYZ
Toronto
MDW
Chicago
S$512 Return, found 3 days ago
S$512
Return
found 3 days ago
Select Delta flight, departing Wed, 6 Aug from Toronto to Chicago, returning Wed, 13 Aug, priced at S$512 found 3 days ago
Delta
Wed, 2 Jul - Sun, 10 Aug
YYZ
Toronto
MDW
Chicago
S$525 Return, found 1 day ago
S$525
Return
found 1 day ago
Select Delta flight, departing Wed, 2 Jul from Toronto to Chicago, returning Sun, 10 Aug, priced at S$525 found 1 day ago
Delta
Sun, 16 Nov - Tue, 18 Nov
YYZ
Toronto
MDW
Chicago
S$544 Return, found 3 days ago
S$544
Return
found 3 days ago
Select Delta flight, departing Sun, 16 Nov from Toronto to Chicago, returning Tue, 18 Nov, priced at S$544 found 3 days ago
Delta
Fri, 24 Oct - Fri, 31 Oct
YYZ
Toronto
MDW
Chicago
S$555 Return, found 18 hours ago
S$555
Return
found 18 hours ago
Select Delta flight, departing Fri, 24 Oct from Toronto to Chicago, returning Fri, 31 Oct, priced at S$555 found 18 hours ago
Delta
Sun, 20 Jul - Sun, 10 Aug
YYZ
Toronto
MDW
Chicago
S$556 Return, found 23 hours ago
S$556
Return
found 23 hours ago
Select Delta flight, departing Sun, 20 Jul from Toronto to Chicago, returning Sun, 10 Aug, priced at S$556 found 23 hours ago

Find the cheapest month to fly from Toronto (YYZ) to Chicago (MDW)

June is typically the cheapest month to fly

From S$271 - S$655 per traveller.

Graph displaying average flight prices per month

Toronto to Chicago route information
Origin airport
Pearson Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
S$296
Distance
692 km

Perfect flights from Toronto to Chicago

Your Journey from Toronto to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Toronto to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, WestJet. Our selection of flights from Pearson Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Toronto to Chicago Flights

Experience the joy of finding cheap flights from Pearson Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$179 and roundtrip prices from S$297*.
 

Pre-Flight Essentials

Ensure a smooth journey from Toronto to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Toronto to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Toronto to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Toronto to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Toronto to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Toronton Pearson to MDW?
Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip flights from YYZ to Midway Intl. Airport (MDW) start from S$297. Book today to secure the best price for your exciting adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Toronton Pearson to Chicago Airport?
This can differ from airline to airline, as each has its own set of terms and conditions. Visit the Customer Service Portal, where there are simple instructions on how to cancel your flight online.
How do I find cheap flights from Toronto Pearson Airport to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from YYZ to Midway Intl. Airport (MDW)?
The flight distance from Pearson Intl. Airport (YYZ) (YYZ) to Midway Intl. Airport (MDW) (MDW) is 700 kilometres. You'll be walking down the air bridge and picking up your bags from the carousel in no time.
Which airlines fly direct from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW)?
At the moment, no airlines offer direct flights from Pearson Intl. Airport (YYZ) to Chicago Airport. You'll have to book a flight with one or more stops. To get the best connections and price, lock in your airfare ahead of time.
Are Pearson Intl. Airport (YYZ) to MDW flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally pick up a bargain, with some of the cheapest fares from Toronton Pearson to MDW arising a few weeks prior to the departure date. If you'd rather plan ahead of time, Expedia compares and updates all the best flight deals continuously --- as early as 12 months in advance in some cases. It does depend on the carrier though, as not every airline advertises prices that far in advance.

Explore a world of travel with Expedia

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